Pyrrolidine → Ethyl 2-amino-1-benzothiophene-3-carboxylate

Participants

Reaction Steps

To a solution of 1b (1.06 g, 4.03 mmol) in toluene (100 mL) was added pyrrolidine (5 mL). The resultant mixture was heated at 100° C. for 8 h, diluted with brine solution (200 mL) and extracted with ethyl ether (300 mL, 3×). The combined organic phases were dried over MgSO4, filtered, and concentrated. Flash chromatography (hexanes/ethyl acetate, 4:1) then afforded the title compound (0.76 g, 85%) as a yellow solid: MS (ES) m/z 222 (M+H)+; 1H NMR (400 MHz, CDCl3) δ8.14 (d, J=8.0 Hz, 1H), 7.53 (d, J=7.2 Hz, 1H), 7.28 (m, 1H), 7.04 (m, 1H), 6.51 (brs, 2H), 4.45 (q, J=7.2 Hz, 2H), 1.50 (t, J=7.2 Hz, 3H).

Provenance & Evidence